#------------------------------------------------------------------------------ #$Date: 2019-11-10 18:58:13 +0200 (Sun, 10 Nov 2019) $ #$Revision: 225969 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/51/58/4515877.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4515877 loop_ _publ_author_name 'Pagliari, Anderson B.' 'Orlando, Tain\'ara' 'Salbego, Paulo R. S.' 'Zimmer, Ge\'orgia C' 'H\"orner, Manfredo' 'Zanatta, Nilo' 'Bonacorso, Helio G.' 'Martins, Marcos A. P.' _publ_section_title ; Supramolecular Packing of a Series of N-Phenylamides and the Role of NH···O=C Interactions. ; _journal_issue 10 _journal_name_full 'ACS omega' _journal_page_first 13850 _journal_page_last 13861 _journal_paper_doi 10.1021/acsomega.8b01801 _journal_volume 3 _journal_year 2018 _chemical_formula_sum 'C11 H15 N O' _chemical_formula_weight 177.24 _chemical_name_systematic ; N-(Phenyl)-2,2,2-trimethylacetamide ; _space_group_IT_number 29 _space_group_name_Hall 'P 2c -2ac' _space_group_name_H-M_alt 'P c a 21' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_block_doi 10.5517/cc81btf _audit_creation_method SHELXL-97 _audit_update_record ; 2004-05-21 deposited with the CCDC. 2015-10-13 downloaded from the CCDC. ; _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.969(3) _cell_length_b 10.642(3) _cell_length_c 10.172(3) _cell_measurement_reflns_used 48 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 19.0 _cell_measurement_theta_min 17.4 _cell_volume 1079.1(5) _computing_cell_refinement 'Stoe DIF4' _computing_data_collection 'Stoe DIF4' _computing_data_reduction 'Stoe X-RED' _computing_molecular_graphics PLUTON _computing_publication_material SHELXL-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Stoe-Stadi-4 4-circle diffractometer' _diffrn_measurement_method 'Profile fitted scans 2\q/\w=1/1' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0139 _diffrn_reflns_av_sigmaI/netI 0.0122 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 2 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 1664 _diffrn_reflns_theta_full 22.47 _diffrn_reflns_theta_max 22.47 _diffrn_reflns_theta_min 1.91 _diffrn_standards_decay_% 12% _diffrn_standards_interval_time 240 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_T_max 0.9896 _exptl_absorpt_correction_T_min 0.7445 _exptl_absorpt_correction_type none _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.091 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'Thin needle' _exptl_crystal_F_000 384 _exptl_crystal_size_max 4.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.148 _refine_diff_density_min -0.110 _refine_diff_density_rms 0.039 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.6(19) _refine_ls_extinction_coef 0.211(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 125 _refine_ls_number_reflns 1408 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.123 _refine_ls_R_factor_all 0.0387 _refine_ls_R_factor_gt 0.0368 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+0.0588P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0902 _refine_ls_wR_factor_ref 0.0924 _reflns_number_gt 1352 _reflns_number_total 1408 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ao8b01801_si_003.cif _cod_data_source_block g15 _cod_depositor_comments ; The following automatic conversions were performed: data item '_symmetry_cell_setting' value 'Orthorhombic' was changed to 'orthorhombic' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas ; _cod_original_sg_symbol_H-M Pca2(1) _cod_database_code 4515877 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' '-x, -y, z+1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags C1 C 0.10825(19) 0.13102(19) 0.18540(18) 0.0675(5) Uani 1 1 d . C2 C 0.0440(2) 0.0795(3) 0.0617(2) 0.0990(8) Uani 1 1 d . H2A H -0.0359 0.0339 0.0844 0.139 Uiso 1 1 calc R H2B H 0.1057 0.0241 0.0182 0.139 Uiso 1 1 calc R H2C H 0.0213 0.1476 0.0041 0.139 Uiso 1 1 calc R C3 C 0.0124(2) 0.2209(3) 0.2539(4) 0.1073(9) Uani 1 1 d . H3A H -0.0695 0.1778 0.2745 0.150 Uiso 1 1 calc R H3B H -0.0065 0.2906 0.1970 0.150 Uiso 1 1 calc R H3C H 0.0529 0.2511 0.3336 0.150 Uiso 1 1 calc R C4 C 0.1431(3) 0.0211(2) 0.2776(3) 0.0987(8) Uani 1 1 d . H4A H 0.0646 -0.0291 0.2923 0.138 Uiso 1 1 calc R H4B H 0.1750 0.0535 0.3599 0.138 Uiso 1 1 calc R H4C H 0.2117 -0.0297 0.2380 0.138 Uiso 1 1 calc R C5 C 0.23590(19) 0.20316(16) 0.1489(2) 0.0579(5) Uani 1 1 d . O6 O 0.26366(15) 0.22817(14) 0.03514(14) 0.0794(5) Uani 1 1 d . N7 N 0.31449(16) 0.23892(14) 0.25012(17) 0.0603(4) Uani 1 1 d . H7N H 0.285(2) 0.2272(18) 0.330(3) 0.072 Uiso 1 1 d . C8 C 0.43706(17) 0.30647(15) 0.24210(19) 0.0573(5) Uani 1 1 d . C9 C 0.5224(2) 0.2961(2) 0.1359(2) 0.0765(6) Uani 1 1 d . H9 H 0.4990 0.2458 0.0648 0.092 Uiso 1 1 calc R C10 C 0.6424(2) 0.3606(3) 0.1355(3) 0.1035(9) Uani 1 1 d . H10 H 0.6994 0.3537 0.0635 0.124 Uiso 1 1 calc R C11 C 0.6785(3) 0.4342(3) 0.2391(5) 0.1146(10) Uani 1 1 d . H11 H 0.7594 0.4778 0.2377 0.138 Uiso 1 1 calc R C12 C 0.5946(3) 0.4436(2) 0.3460(3) 0.1006(9) Uani 1 1 d . H12 H 0.6195 0.4930 0.4173 0.121 Uiso 1 1 calc R C13 C 0.4734(2) 0.38015(19) 0.3483(3) 0.0749(6) Uani 1 1 d . H13 H 0.4169 0.3870 0.4207 0.090 Uiso 1 1 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0656(11) 0.0923(13) 0.0446(10) -0.0049(9) 0.0012(9) -0.0214(10) C2 0.1017(16) 0.132(2) 0.0638(14) -0.0054(13) -0.0082(12) -0.0550(16) C3 0.0628(12) 0.147(2) 0.112(2) -0.031(2) 0.0123(15) -0.0180(13) C4 0.1092(17) 0.1079(16) 0.0789(16) 0.0176(14) 0.0003(13) -0.0401(14) C5 0.0618(10) 0.0755(10) 0.0364(10) -0.0015(9) 0.0011(8) -0.0089(8) O6 0.0746(9) 0.1252(12) 0.0382(9) 0.0024(8) 0.0006(7) -0.0271(8) N7 0.0621(9) 0.0813(9) 0.0375(8) -0.0001(7) -0.0033(7) -0.0121(7) C8 0.0558(9) 0.0597(9) 0.0562(11) 0.0051(8) -0.0130(9) -0.0024(8) C9 0.0641(12) 0.0916(13) 0.0737(14) 0.0062(12) 0.0000(11) -0.0129(10) C10 0.0680(14) 0.123(2) 0.119(2) 0.0225(19) 0.0016(14) -0.0194(14) C11 0.0763(14) 0.0954(16) 0.172(3) 0.013(2) -0.032(2) -0.0269(14) C12 0.0910(16) 0.0765(13) 0.134(3) -0.0127(15) -0.0507(19) -0.0044(13) C13 0.0723(12) 0.0710(12) 0.0813(13) -0.0089(10) -0.0280(11) 0.0031(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 C1 C3 110.0(2) C2 C1 C5 109.38(16) C3 C1 C5 108.51(16) C2 C1 C4 109.05(19) C3 C1 C4 109.9(2) C5 C1 C4 109.92(16) C1 C2 H2A 109.5 C1 C2 H2B 109.5 H2A C2 H2B 109.5 C1 C2 H2C 109.5 H2A C2 H2C 109.5 H2B C2 H2C 109.5 C1 C3 H3A 109.5 C1 C3 H3B 109.5 H3A C3 H3B 109.5 C1 C3 H3C 109.5 H3A C3 H3C 109.5 H3B C3 H3C 109.5 C1 C4 H4A 109.5 C1 C4 H4B 109.5 H4A C4 H4B 109.5 C1 C4 H4C 109.5 H4A C4 H4C 109.5 H4B C4 H4C 109.5 O6 C5 N7 122.08(17) O6 C5 C1 121.86(16) N7 C5 C1 116.05(17) C5 N7 C8 126.79(18) C5 N7 H7N 118.5(16) C8 N7 H7N 114.4(15) C9 C8 C13 119.69(18) C9 C8 N7 122.36(18) C13 C8 N7 117.9(2) C8 C9 C10 119.9(2) C8 C9 H9 120.1 C10 C9 H9 120.1 C11 C10 C9 120.8(3) C11 C10 H10 119.6 C9 C10 H10 119.6 C10 C11 C12 119.5(2) C10 C11 H11 120.2 C12 C11 H11 120.2 C11 C12 C13 120.6(2) C11 C12 H12 119.7 C13 C12 H12 119.7 C8 C13 C12 119.5(2) C8 C13 H13 120.3 C12 C13 H13 120.3 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.515(3) C1 C3 1.521(3) C1 C5 1.532(3) C1 C4 1.539(3) C2 H2A 0.9600 C2 H2B 0.9600 C2 H2C 0.9600 C3 H3A 0.9600 C3 H3B 0.9600 C3 H3C 0.9600 C4 H4A 0.9600 C4 H4B 0.9600 C4 H4C 0.9600 C5 O6 1.219(2) C5 N7 1.348(3) N7 C8 1.420(2) N7 H7N 0.87(3) C8 C9 1.379(3) C8 C13 1.383(3) C9 C10 1.379(3) C9 H9 0.9300 C10 C11 1.362(5) C10 H10 0.9300 C11 C12 1.375(5) C11 H11 0.9300 C12 C13 1.384(3) C12 H12 0.9300 C13 H13 0.9300 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion C2 C1 C5 O6 10.3(3) C3 C1 C5 O6 -109.8(2) C4 C1 C5 O6 130.0(2) C2 C1 C5 N7 -170.69(19) C3 C1 C5 N7 69.2(2) C4 C1 C5 N7 -51.0(2) O6 C5 N7 C8 -0.9(3) C1 C5 N7 C8 -179.92(17) C5 N7 C8 C9 -30.5(3) C5 N7 C8 C13 152.58(19) C13 C8 C9 C10 -0.9(3) N7 C8 C9 C10 -177.71(19) C8 C9 C10 C11 0.3(4) C9 C10 C11 C12 0.5(4) C10 C11 C12 C13 -0.7(4) C9 C8 C13 C12 0.6(3) N7 C8 C13 C12 177.59(18) C11 C12 C13 C8 0.2(3)